Regio- and stereoselectivity in the cyclization of enolates derived from 4,5-, 5,6-, and 6,7-epoxy-1-phenyl-1-alkanones. Competition between C- and O-alkylation
✍ Scribed by Paolo Crotti; Valeria Di Bussolo; Lucilla Favero; Franco Macchia; Mauro Pineschi; Elio Napolitano
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 852 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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Molecules of the title compound, C 18 H 14 N 2 O 6 , are linked into chains by a combination of one CÐHÁ Á ÁO and one CÐ HÁ Á Á%(arene) hydrogen bond, augmented by a dipolar carbonyl±carbonyl interaction.
## Abstract The __C__ methylation of the carbohydrate‐derived __O__‐chiral esters 5a‐d to derivatives 8 proceeds with (__R__) selection of 1:1 to 10:1 and depends primarily on the base used for enolate generation. Lithium 2,2,6,6‐tetramethylpiperide (LTMP) shows the highest and lithium hexamethyldi